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Question about TTMs and Stamps

Ok so I've sent some TTM e-mail requests and have had some success. I have a few 8x10s that I'd like to mail out to players such as Dirk Nowitzki and Peyton Manning. My question is how do I find out the proper postage that I am supposed to use for my SASE as well as outside envelope that the SASE and 8x10 will be in? Any help would be greatly appreciated

Take it once, get it weighed, then, as long as you send them the same way each time, just use the same postage. I pack different 8x10s differently, and sometimes include a sharpie or pen, so I usually let the PO figure it out for me.